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First example of Diels-Alder reaction in the 2,3,4,4a-tetrahydroquinoline series. Synthesis of hydrogenated 5,8-ethanoquinolines |
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| Authors: | Eugeniya V Nikitina Dmitry G Grudinin Vladimir V Kouznetsov |
| Institution: | a Organic Chemistry Department, Russian Peoples Friendship University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation b Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow 119991, Russian Federation c Valeant Canada Ltd, 1956 Bourdon St., Montréal, QC H4M 1V1, Canada d Department of Chemistry, University of Douala, Faculty of Sciences, PO Box 24157, Douala, Cameroon e Laboratorio de Química Orgánica y Biomolecular, CIBIMOL, Escuela de Química, Universidad Industrial de Santander, A.A. 678 Bucaramanga, Colombia |
| Abstract: | Diels-Alder reactions in the 2,3,4,4a-tetrahydroquinolines series were studied for the first time. It was shown that these dienes demonstrate only moderate reactivity. 4+2] Cycloaddition occurs stereo- and regioselectively only for alkenes bearing an electron-withdrawing group (acrylonitrile, maleic anhydride, dimethyl acetylene dicarboxylate, methyl propiolate). In this case, endo-Diels-Alder adducts, spiroannelated 5,8-ethanoquinolines, are formed in a high yield. Cyclopentadiene, being a highly reactive diene component, reacts with 2,3,4,4a-tetrahydroquinolines as the dienophile. Electron-rich unsaturated compounds (N-vinylpyrrolidone, vinylethyl ether, phenylacetylene) are inert to this cycloaddition reaction. |
| Keywords: | Diels-Alder cycloaddition 2 3 4 4a-Tetrahydroquinolines 5 8-Ethanoquinolines 7 12-Ethenoquino[6 7-f]quinolines |
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